Novel syntheses of densely functionalized indolizines, di- and tetrahydroindolizines from 2-formyl-1,4-dihydropyridine systems based on cascade process

Several indolizines, di- and tetrahydroindolizines have been synthesized successfully in a one-pot procedure, in two or three steps from 2-formyl-1,4-dihydropyridine derivatives and malonitrile in 57–87% yield. The general mechanism leading to these azacyclic compounds, involving 2-dicyanovinyl-1,4-...

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Bibliographic Details
Published in:Tetrahedron letters 2001-08, Vol.42 (33), p.5663-5667
Main Authors: Marchalı́n, Štefan, Cvopová, Katarı́na, Pham-Huu, Duy-Phong, Chudı́k, Miloslav, Kozisek, Jozef, Svoboda, Ingrid, Daı̈ch, Adam
Format: Article
Language:English
Subjects:
cascade process
dihydroindolizines
dihydropyidines (DHP)
indolizines
stereoselectivity
tetrahydroindolizines
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Summary:Several indolizines, di- and tetrahydroindolizines have been synthesized successfully in a one-pot procedure, in two or three steps from 2-formyl-1,4-dihydropyridine derivatives and malonitrile in 57–87% yield. The general mechanism leading to these azacyclic compounds, involving 2-dicyanovinyl-1,4-dihydropyridines, is discussed. An original approach to highly substituted indolizines, di- and tetrahydroindolizines from 2-formyl-1,4-dihydropyridines derivatives was described in a one-pot procedure by the tandem Knoevenagel condensation/amino–nitrile cyclization.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01054-1